Control and Release
by TheCleverDame
Summary: TEDTalk!Sam - After the rest of the staff is caught in a snowstorm, you find yourself acting as a personal assistant to the notorious Sam Winchester. As the arrangement becomes more defined, you and Sam begin a sexual adventure with dangerous consequences. - Dom/Sub, humiliation, embarrassment, sexual objectification, mutual masturbation, spanking, cum play, fingering, anal play.
1. Chapter 1

This story is based on TEDTalk!Sam from episode 14.13

* * *

"No way!" You close your eyes. This has to be a nightmare.

"You're the only person who made it to the hotel. We're all snowed in until morning, no one can get a flight out. You're going to have to staff him until I get there. His schedule is pretty light compared to what it usually looks like. Half his meetings were canceled because of the storm." Pepper rattles into the phone. She's only a year or two older than you but she's your boss's boss. She's Sam's executive assistant, in charge of the entire assistant staff and she's had it out for you since you started four months ago.

"I don't think I can do this." You gulp, shrugging your jacket off. You deliver mail and push the coffee cart around the building, the lowest rung on the corporate ladder.

"You don't have a choice." She snips. "You think this is what I want? I'm going to end up paying for this, even though it's not even remotely my fault. I can't control the weather…look I'm going to send you his schedule. Just make sure he's on time. He'll let you know if you're doing something wrong, believe me. Just keep your mouth shut and do what he tells you to do. Whatever you do, don't cry. He hates it when people cry."

"Why would I cry?" You regret answering the phone and you already know the answer to your question.

Sam Winchester is a real son-of-a-bitch and everyone knows it.

To say his reputation proceeds him would be a gross understatement. He's smart, successful, ruthless and above all, focused. You've worked for Winchester and Singer for six months and have yet to encounter him.

You've never even directly spoken to him, never seen him in person other than the monthly reviews he conducts with the entire company in attendance. Even then he's just a man on a stage.

"I'm emailing you right now. Keep a copy of the schedule on you at all times." She pauses to take a breath. "Are you listening to me?"

"Yeah, I'm listening. Have the schedule on hand, keep my mouth shut, and try not to burst into tears."

"Just don't fuck this up." Pepper is as over-worked as everyone on the executive level. You can't really blame her. This job is her life. "You need to check in with him tonight. Just knock on his door and ask if he needs anything. He'll send you away, but he expects a check in just to be sure."

"Okay." You nod to yourself in a windowless hotel room. "I can do this."

The elevator rises slowly to the penthouse floor of the Ambassador Hotel. It's nearly midnight and his flight arrived only an hour ago. He was in Tokyo last week and was rerouted during the storms in Boston.

You knock twice on his door, waiting with bated breath and hoping he won't answer. You're about to leave when the deadbolt turns and the door opens to reveal Sam Winchester with a cell phone up to his ear. He pauses for a moment, looking you over head to toe before opening the door the rest of the way and walking away chattering to whoever is on the other line.

You stand in the hallway, unsure if the open door is an invitation. On cue he turns around, eyes narrowing as his nods his head.

Already off to a rough start.

Shutting the door behind you, you follow him into the living room, standing awkwardly, waiting for his call to end. When he finally hangs up, he presses his phone against his chest, staring at you like a zoo animal. "Pepper said you're the only employee here?"

"Y-yes." You choke out. "I was visiting family in New Mexico, so I flew in from-"

"We'll have to make due I guess." He cuts you off. "You have tomorrow's schedule?"

"Ahuh." You hold up your phone, forcing a smile.

"Ahuh?" He tilts his head. "I prefer actual words. Yes or no."

Your cheeks flush hot, embarrassment settling in.

"Yes, Mr. Winchester." You correct. "I have your schedule. Pepper asked me to check in and see if you need anything tonight."

"No. I don't need anything." His stare is unrelenting. "Do you have something more appropriate to wear tomorrow?"

His question takes you off guard as you look down at the sweatshirt and jeans you're currently wearing. "I, um, yes sir."

There's a nauseating combination of shame and anger settling into your gut. He really does live up to his reputation.

"Good. You better go. We have an early start tomorrow. I won't need you until after the gym. I'll be done by 6:15 and I expect you to be here."

"Yes, sir." You nod, looking at anything but his face. You're an ant under a microscope, already feeling the heat.

"Good. You can go now." He pulls out his phone, hits a number and begins speaking to someone in Japanese as you high tail it out of the room.

You don't cry until you're in the elevator. The doors shut as you fight back the urge to turn into a sobbing mess, instead of wiping away a few tears and composing yourself.

Three hours of sleep is all you manage. Between your nerves and being afraid you'll sleep through the alarm, you're up and showered at four and dressed by five.

Clutching a portfolio in your arms you step off the elevator. There's a full-length mirror at the end of the hallway and you stop to make sure you're presentable. You thought you'd be manning a promotional table during the conference, planned on wearing khakis and a pullover. You brought exactly one business professional outfit that you haven't tried on in a year or two. It's a plum-colored sleeveless sheath dress that's tighter than you would prefer. It looks good but perhaps a little much for this trial by fire.

"This is as good as it gets." You whisper, giving yourself a final look before finding Sam's room.

You knock and he answers immediately, holding his glasses in hand.

"You're late." He quips, turning around to gather his suit jacket and briefcase.

"I," You stop, checking your phone. "It's 6:15."

"In my world on time is late and early is expected."

"I'm sorry." You're horrified. "I didn't - I'm sorry."

"I don't want an apology. I want you to do better next time." He eyes settle on your bare shoulders, then tick down to rest of your body. It's a quick glance but you catch him. "I have files in the living room. Please make sure everything is in order and ready to go. Pack it all up, we don't want to leave anything to chance."

You wordlessly scamper around the room, carefully collecting half used notepads and countless pages of legal discourse that you couldn't understand if your life depended on it. When you turn back around, clutching his files in your arms, he's leaning against the doorframe between the entryway way and the living area, watching you intently.

Your cheeks burn hot. Sam is handsome, there's no arguing that fact, but he's also notoriously difficult to work for. You've never once heard even a whisper that he mixes business with pleasure. If anything he's known for being controlled. Everyone's heard of his type, high-level business execs that are uptight beyond belief.

But the way he's looking at you…no. It's in your head.

"I've got everything." You nod, shoving the files into your leather bag.

"Good, I want to get down there early." He checks his watch and strides out of the room without another word and you're left scrambling after him. Instead of heading to the public elevator you took earlier, he turns in the opposite direction to head toward the private lift his penthouse room offers as a perk. You stand beside him as the doors close and he pushes the button for the ground level.

He turns toward you, looking concerned. "I asked you to wear something business professional."

"I-" The humiliation continues. "I am. This is all I brought with me."

"I see." His eyes narrow.

"Would you like me to go grab a sweater to wear over it?" You ask softly.

"No." He purses his lips, head tilting ever so slightly. "I wouldn't be able to tell how tight your dress is if I couldn't see your panty line."

You nearly choke on your own spit. Letting out a nervous cough as your breath speeds up. You force yourself to look at him, trying your damnedest to determine what this is. Is he coming on to you? Just a perfectionist who's so caught up in the details that the outline of your lace underwear crosses some sort of invisible line?

"I didn't realize you could see. I'm sorry." You stare at the floor, praying to God this day ends quickly.

"Don't be sorry." He commands tone calm and even. "Take them off."

The world stops. All the oxygen evaporates out of the room.

Your eyes go wide, shooting up to meet him and his expression is unreadable. In a split second, your body reacts against your will, heat blooming between your legs, shame tightening in your chest.

You wonder if he's like a predator able to smell fear. Does he somehow know what kind of effect this will have on you? Is it the way you called him sir, or how quickly you responded to his commands?

"You want me to…" You can't finish the sentence but he doesn't need you to.

"Take them off." He repeats.

"Right now…here?" You whisper.

"Yes." He confirms, reaching out to take the bag from you.

You hesitate, but only for a second before reaching under your dress and hooking both hands in your panties. The elevator is nearly at the first floor, and sweat breaks out over your entire body at the idea of being caught.

Stepping out of your panties you hold them up, looking at him like a deer in the headlights. There's nowhere to put them, you didn't bring a purse, the conference is in the hotel so you left it the room. But Sam casually plucks them from your hand and stuffs them into the pocket of his suit pants as the elevator reaches the lobby and the doors slide open with a ding.

"Try to keep up." He hands you back his briefcase, your messenger bag of files, and steps out into the general population as you follow.


	2. Chapter 2

You're sitting next to Sam Winchester, the man that Forbes called one of the most powerful men in business…and he's got your panties tucked in his pocket like it's no big deal.

For the last twenty minutes, you've been gaslighting yourself.

Maybe you read the situation wrong? What if he didn't even mean for you to take off your underwear in the elevator? But the more you replay the incident over and over in your mind you know it really happened. It's a fact that's only confirmed as you shift in the chair and feel your naked ass against the fabric of the dress.

"Y/N." It's Sam saying your name and snapping his fingers that brings you out of this daze.

"I'm so sorry." You gasp, staring from Sam to the other man in the room.

"Do we have the third quarter prospectus or not?" Sam raises his eyebrow and you fish through the folder in front of you.

"Yes." Sliding a copy of the analysis toward both men. "There are future projections on the second page."

You've memorized every detail of the emails Pepper sent. While you don't understand the actual content, you've at least memorized what each meeting requires.

"Thank you." Sam's tone is less than understanding and the man across the table chuckles.

"What happened to your old assistant."

"She's couldn't be here." Sam's eyes don't leave the report in front of him as they talk about you like you're not even here. "We're just working with whatever asset we have, however poor that may be."

The guy snorts and you turn beet red, fight back a swell of emotion. He's just…mean.

You listen to them drone on and on about the future of intellectual property rights and their shared hatred for Jeff Bezos. It's almost one o'clock by the time the meeting is wrapping up. That leaves an hour before he needs to meet with his financial team, the first employees on the ground since the storm passed.

"Are you hungry?" Sam asks succinctly, taking off his glasses and tucking them into his suit jacket.

"Yeah - I mean, Yes. I'm starving." You collect his handwritten notes, carefully packing them into his briefcase.

"Good, we've got time to sit down for a meal. The restaurant here is supposed to be at least tolerable."

–

Sam's enthralled with his phone and you're just happy to have his attention elsewhere. You watch as the wait staff carries trays of food in both directions. You haven't eaten in twenty-four hours and all you want is the juicy burger that just walked by.

Your waiter is a young, happy guy who bounces over to the table. While he might not know who Sam is, he knows money when he sees it, occupational hazard.

"Welcome." He clasps his hands together. Sam sets his phone on the table, offering his full attention. "Can I get you started with a drink? We have several white wines that are perfect for a light lunchtime-"

"No," Sam grimaces. "Two waters and we'll need to order now. We're on a tight schedule."

"Sure, of course." The waiter gestures toward the menu. He turns toward you, "Do you know what you'd like ma'am?"

You can practically taste the burger. "Definitely, I want-"

"She'll have the blood orange and spinach salad, and I'll have red quinoa and avocado." Sam looks across the table, closing his menu. The waiter hesitates, looking between you and Sam, who clears his throat. "That's all."

You sit back in your seat, clenching your fist under the table. What is this? Your first instinct is that this a test. He's systematically testing your limits like a raptor testing the fence in Jurassic Park. He wants to see how far he can push. His comments about your clothes, the panties, his snide remarks in the meeting and now ordering your lunch - he wants to find out how much you'll take.

It's his motives you're unsure about. Is he interested in you sexually or is all this just his sick version of a power game?

"Thank you," you smile sweetly. "I was going to order a salad but I couldn't decide which one."

His eyes narrow, resting a forearm on the table. "It's important to take care of your body."

There it is, something dark simmering right under the surface This guy has boatloads of pent up issues, he's going to make some therapist a lot of money one day.

"I agree." You sit up straight, folding the cloth napkin over your lap.

"Do you?" He's grinning but his eyes are honed in on you like a snake sizing up a fat little mouse. "Do you exercise?"

"Ye-yes." You catch yourself this time. Normally you're pretty good at faking confidence when you can't muster the real thing but Sam is getting under your skin. "I used to be a runner, but I hurt my knee a couple years back. Now it's all pilates and yoga."

"How old are you?" His thumb and middle finger slide over each other as his studies you.

"Twenty-eight." You take a drink of water just to break the intensity of his focus.

"And how did you end up working for me?"

"I just, I needed some office experience. I've never really worked in a professional environment before. I'm just trying to get my life on track, or least headed one solid direction. Look, I shouldn't be here. I deliver the mail. I'm no one, Mr. Winchester."

His throat bobs when you call him Mr. Winchester, a smile tugging at the corners of his mouth.

"I think you're someone." His eyes drag over you again, like you're a piece of meat. There is no mistaking he wants something more from you than note taking. "Do I make you nervous?"

"Yes." You respond succinctly. "I don't know what you want - I'm not sure how to react."

"You're doing fine so far."

"Yeah, right," you sigh, looking up at the ceiling. "I'm terrible at this. I'm not organized, I don't know what I'm doing and you have standards that are beyond-"

"I don't care about that." He waves his hand, that calm demeanor never breaking. "You're not the most organized assistant, but Pepper will be here by tonight. She'll fix whatever you manage to fuck up."

You swallow, staring in silence as a waitress brings your salads. Once you're alone again you lean in closer, placing both hands palm down on the table. "Why are you doing this?"

"What am I doing?" He asks, forking leafy greens, glancing up as an afterthought.

"The way you talk to me. In the elevator when you -" You whisper, making sure no one can hear you. "You have my underwear in your pocket."

"Do you need them back?" He sets down his fork.

"What?" That wasn't the response you expected.

"If you need them, I'll give them to you." He offers.

"I don't understand this. You're…" your point at him. "You. You don't know anything about me. I could sue you for sexual harassment."

"Are you going to sue me?" He's clearly unconcerned. "Let me ask you a question, Y/N. Why do you think I've been so successful?"

Clasping hands together in your lap you think carefully, trying to suss out if this was a trick question. "You're smart, focused. You work hard."

"None of those really matter in the long run. The reason I've gotten to where I am today is that I can read people. My dad was a ringer, but I'm even better at it. You give me two minutes with anyone and I'll tell you what you want and if they're telling the truth. Everyone has a tell, it's the little ticks and unconscious responses that give people away."

"Like poker." You add and he seems happy you made the connection.

"Yes, something like that. Last night when you came to my room you were nervous, unsure of yourself. But the moment I corrected you, told you to use your words, you start breathing faster, pupils dilated. You do the same thing every time you call me Mr. Winchester."

"In the elevator, it was more than just your eyes and your breath. Your whole body went flush and lips parted. Every inch of you liked being given orders. You see, most people don't like how direct I am. I hurt feelings, burn a lot of bridges. But you are a rare creature. You enjoy the degradation."

"Well," you start, closing your eyes in a flawed attempt to keep your cheeks from burning bright red. "I don't know that I would say I enjoy it."

"Tell me," he pulls back a little, talking to you as if you're the only two people in the room. "Are you wet right now?"

The question alone makes your thighs clench together. You stare at him for a moment before answering.

"Yes." The confession comes out as a whimper.

He smirks, refocusing on his meal. "Eat your lunch. We have a long afternoon."

After seven hours of meetings and glad-handing, you're grateful the day is coming to an end. Everyone wants to meet Sam, talk to him, pitch their ideas and make a connection. Everyone wants a piece of him and you've spent the day trying to note down the name and position of every person he spoke to.

It's a little after eight as you trail behind him, lugging his briefcase back up to his room.

"Pepper's here." He looks up from his phone, fishing his room card from his pocket. "She'll take over for the cocktail hour tonight."

"Perfect." You sigh. You weren't sure you had the stamina to make it through the rest of the night.

"Do you want to come inside?" He asks, pushing the door open, stepping out of the way.

"No." You avoid his eyes. "I'm gonna go to my room."

"Are you sure?" His head tilts to the side.

"Yes." You carefully set his briefcase at his feet. "Goodnight."

"Y/N." He says your name with such finality that it sends a shiver up your spine. "Come inside."

"I said I didn't want to." You meet his stare as your hands begin to shake. "We shouldn't-"

"And I told you to come inside." His jaw clenches when you hesitate. "Now."

"Okay." You squeak stepping into the room. The door shuts behind you immediately, and there's the click of the deadbolt.

"In here." He disappears through a doorway and you follow into the master suite. The moment you lay eyes on his bed a warmth bubbles up from your belly. You hate that there's any part of you that responds to him like this.

Sam circles around you, keeping his distance as he takes a seat in the chair in the corner of the room.

"What do you want from me?" You ask, barely able to stand on quivering legs.

"I want you to sit on the bed." He explains, leaning back in the chair. His mouth is a tight line, betraying nothing. If he has any particular feelings one way or the other you'd be the last to know.

"Okay." You whisper, sitting gingerly on the edge of the bed, watching him watch you.

"Unzip your dress." His instruction is enough to take the air right out of your chest. He must be enjoying this level of control, but you'd never know from looking at him.

You reach behind your shoulders and manage to unzip the back, looking to him for further orders.

"Pull it down around your waist." One large hand palms over the crotch of his slacks, giving the first indication that he's getting any actual pleasure.

You comply, pulling your arms out and lowering the top half of the dress until it's bunched below your breasts, exposing a lace, black bra.

"Pull your bra down. Show me your nipples." His eyes shift down to watch.

Oh, God.

You tug each cup down until both breasts are exposed. Your nipples are already hard as pebbles, aching along with the rest of your body.

"Pull your skirt up around your thighs." He watches as your eyes fall to his hand, rubbing his cock through his pants. You comply, pulling your skirt up. "Further."

By the time he's satisfied your dress is up around your hips, bare ass on the soft comforter.

"Now lie back and spread your legs."

You stare at each other for a moment before you lean back, the back of your head meets the mattress. You suck in a fractured breath, spreading your thighs until you feel the cool air on your sex.

"Wider." He's a disembodied voice now. Measured and confident in every detail of what he wants from you. "Let me see your pussy."

You bend your knees, putting your heels on the bed until they touch your buttocks, spreading yourself as wide as possible for his viewing pleasure.

"Your cunt's as perfect as the rest of you." He laments, but you get a distinct feeling he's not really talking to you, it's just commentary. "Touch yourself."

You close your eyes for a moment, the ceiling blinking in and out of view as your hand snakes between your legs. Using your middle finger you find your clit and make slow, careful circles, applying just enough pressure to bring yourself pleasure.

This is by far the most humiliating thing you've ever done, but it's the humiliation that has you so worked up. He was right. There's something about the complete shame of the moment that's working you up.

There's a familiar zip and the rustle of clothing, and then the faint, subtle sound of skin on skin as he strokes his cock, watching you masturbate.

The more your body responds, the less you care about the fact that you're rubbing your clit in front of your boss. Dipping into your slick cunt, you coat your finger, moving back to press faster circles over the swollen bud. A muted sigh escapes your lips and you realize you've been trying to stay quiet but there's no reason remain silent. A full moan tears from your throat as you butterfly your legs further apart in an effort to give a better view. At this moment you want him to see every inch of you, to feel his eyes burning into your skin.

"Fuck yourself with your fingers." His voice is strained, a crack in the armor as you hear him stroke himself faster.

You slide your other hand between two shaking thighs and sink two fingers into your pussy. He's breathing faster, harder and the room is filled with the sounds of both your labored breath, the wet noise of your cunt taking your own fingers and Sam working his cock.

"Oh fuck." You moan, arching back into the mattress and shoving a third finger into your aching cunt. Your hand is moving faster and faster over your clit and you're so close to having an orgasm in front of his man you hardly know.

"Put the fingers that are in your cunt, in your mouth, and keep rubbing your clit. Make sure your legs stay open when you cum." He pants, the whap, whap, whap of his hand growing even faster.

You don't hesitate, shoving the three fingers over your tongue, sucking on the taste of yourself as you cum. Groaning, you struggle to keep your thighs spread wide, giving him a full view of your wet, empty flesh clutching around nothing.

He grunts one time, and the sound of his hand stops as you claw at the sheets, trying to anchor yourself as you pant and stare at the ceiling.

For minutes the only sound is your breath. You're not sure what to do, but then he's zipping up as you hear him moving across the floor. "You can leave."

By the time you sit up, he's gone. The door to the bathroom clicks shut, the lock turns as the shower comes on. Leaving you trembling and unsure of what exactly just happened.


	3. Chapter 3

Life goes on, you return to Boston but the events of that night haunt you. There are times when you can't believe it actually happened, that Sam Winchester had you in his room. And there are nights when it's all you can think about, laying in the dark with a hand between your legs pretending he's watching you.

But a week becomes a month and you get the sense that whatever happened was a fleeting mistake. A questionable choice that he'd prefer to forget.

You're in the middle of typing up handwritten notes for one the of the junior partners when the phone rings. Pepper's name pops up and you roll your eyes. She hated you from the beginning but after the conference, she's really had it out for you. She made it clear that you did everything wrong, and she suffered Sam's sour disposition as a result.

"Hello Pepper," you answer, feigning a cheery disposition.

"What did you do?" She hisses, clearly trying to keep her voice down.

"I don't know what that means." You slouch back in your chair, defeated. None of your work is ever good enough for her.

"Well, you better figure it out. He wants you up here, now." She grits out.

An immediate mix of dread and excitement springs to life, making your chest tight and cheeks flushed. Before even fully processing the words, you're sweating.

"Who?" Whispering, you look around, afraid that anyone who sees you might suddenly develop telepathic powers and discover your dirty little secret.

"Who the fuck the do you think? Sam. I don't know what you did but he wants you in his office ASAP."

"Okay." You swallow. "I'm on my way."

The walk to the elevator seems as if you're walking underwater, everything moving in slow motion. You've convinced yourself you'd never see him in person again, or when you did, he'd dismiss you.

What if this is just about work? No, there's no way. You're in charge of the most meaningless, mindless busy-work of anyone in the company. This is him flexing control, you're sure of it. He's ignored you for weeks and out of nowhere, you're being summoned to the executive floor.

"You okay?" Max, a junior associate, and resident hot shot asks stepping in beside you.

"Yeah." You snap, looking at him in sudden concern. "Do I look like something's wrong?"

"You're all-" He points at your face, turning his finger in a circle. "Red. Are you getting sick? If you are, you better go home. The last thing anyone needs is the flu."

"I'm fine." You reach over and hit the button for the top floor.

"You're headed to the attic?" He laughs, hollowing out his cheek with a whistle as if to say glad it's not me. "You screw something up?"

"No, I mean, I don't think so. Why does everyone keep asking me that?"

You know full well that no one of your lowly position gets called up unless they're on the chopping block.

"I've been here a year and I've never been above the twentieth floor." Adjusting his tie Max checks out his reflection in the mirrored wall. "Tell you what, how about I take you out for a drink later? Good or bad, you're gonna need it."

"Maybe." You respond absentmindedly as the elevator dings and Max steps off.

"Good luck." He gives you a little salute as the doors slide shut and you continue your ascent.

The moment you step off the elevator Pepper is there to give you the third degree en route to Sam's office.

"If you did something you have to tell me now so that I get in front of it. Everything falls on me. I don't want to pay the price for your incompetence."

"I honestly have no idea." You wish she'd stop talking, you can barely think at the prospect of seeing him again.

"Oh God," glaring at you she opens the door to his office, gesturing for you enter. "Let me do the talking."

Sam's sitting at his desk, fixated on his computer. When he looks up he immediately hones in on you, glancing at Pepper as an afterthought.

"She's here, finally. I can't imagine what took so long. I called her twenty minutes ago." Lies. "Would you like me to stay?" Pepper asks, grinning unnaturally wide.

"No." Sam quips. "Shut the door and let me know once everyone else is on the call. I don't want to be disturbed."

"Of course." She turns, sneering silently at you before scampering out of the room.

And before you know it, you're alone with him again. You don't say anything, just stand in place as you stare at each other in silence.

"If you want to leave, you should do it now." He explains calmly, sitting back in his chair. "I won't stop you and we'll never speak of it again. But if you stay, you're giving me consent. Do you understand?

"Yes." You force out, the fractured word barely audible.

"And what have you decided?" Tilting his head to the side he looks you over from head to toe.

"I'd like to stay." You're wet already, squeezing internal muscles and fighting the urge to let your eyes flutter shut.

"Good choice." His face is expressionless. For being a savant at reading other people he's just a skilled at cloaking his own emotions. "Come over here."

Your hands shake as you slowly walk to his desk. He motions for you to come around the side so that you're standing right next to his chair.

"Do you have a cell phone?"

"Not with me."

"Bring it with you next time."

"Okay."

"Are you wearing underwear?" There's small tug at the corner of his mouth.

"Yes." You swallow, closing your eyes for a fleeting second.

"Take them off." He watches you reach under your skirt and tug the fabric down your legs. Using one hand to balance yourself on the arm of his chair, carefully stepping out of them one high heel at a time. He holds out his hands and you drop them into his palm. "Don't wear them again."

Jesus Christ.

"I won't." You confirm. Every inch of skin covered in sweat.

"Sit here." He taps the end of the desk with two fingers, his eyes never leaving yours. Perching on the edge of the desk you pray you don't pass out. You can scarcely breathe at the anticipation. "Unbutton your blouse."

His eyes are relentless, boring holes right through you as shaky fingers pop button after button on your creamy, silk blouse. You pull the material open, giving him a view of the bra underneath. His tongue darts out over his lower lip, his line of sight glued to your tits.

"Pull your bra down, just under your nipples." He instructs and you comply. A pattern is forming, he has a definite preference for how you display yourself. His eyes dart up from your breasts. "Pull your skirt up and spread your legs so I can see your cunt."

There's a split second when you don't think you can do this, especially not in his office in the middle of the day with a building full of people. But it's also those facts that turn the fear into excitement, pulsing through your veins.

You stand up long enough to pull your skirt up around your waist, bare pussy on full display as you sit back on the edge of his desk and spread your thighs.

"Lean back and open your legs wider." He commands as you settle onto your elbows, balancing one leg on the handle of his desk drawer, giving him a pornographic view of your sex. "You're wet."

The way he says the words makes it sound like he's a pious priest and you're some kind of wanton harlot.

"I like it when you look at me." You confess, feeling like a whore laid out on his desk with your shirt open and legs spread.

"If you get my desk wet you're going to clean it with your tongue."

Mother Fuck. You could probably cum just like this. You wouldn't even need to touch yourself. Just listening to him say shit like that would eventually be enough.

"Mr. Winchester." Pepper's voice scared you half to death as she hails him on his intercom. "Everyone's on the call, they're waiting for you."

Sam looks at you, grabbing his cock through his pants. "Stay just like that, don't move, don't touch yourself. Just stay open for me. You understand."

"Yes." You nod slowly.

Then he picks up the desk phone and hops on a conference call as if this is the most normal thing in the world.

At first, he's not talking much, just replying with little verbal cues, palming his cock through his pants. He rocks back his office chair, clicking the end of a pen with his thumb and staring at your pussy like the wolf in Little Red Riding Hood. Something on the call sparks his interest because he refocuses on his computer screen, launching into an in-depth explanation about the importance of procedure and process.

Your eyes are closed as you listen to his voice, legs beginning to shake as you keep yourself in the requested position. He's not doing anything, he hasn't come close to touching you, at the moment he's not even looking in your direction, but it's somehow one of the most sexual and arousing situations you've ever been in.

He called you up here to take out your tits, hike up your skirt and present yourself as a piece of erotic art.

The combination of humiliation and arousal has every part of your body on fire. Your nipples are rock hard, throbbing with every beat of your heart, just the same as your clit. You want to close your legs, rub your thighs together to get a small amount of relief. Concentration slipping your legs begin to fall closed and there's an abrupt, hard smack on the inside of your knee, his open palm slapping your skin.

"Fuck," you wheeze, mouth falling open.

The mark stings as you stare at him, watching him rub that same hand over his thigh. There's a red handprint springing to life on your skin, and now it's throbbing right along with the rest of all your sensitive bits. You tense up, clenching your cunt in desperation. If he had any question about how you'd respond he must know the answer now because you're twice as wet as before.

He places a hand over the mouthpiece of the phone, "you're not very good at following the rules."

"I'm trying." You whisper. There's a tear running down your cheek. Perhaps it's from his hand or maybe you're just so fucking turned on that your body is responding in unfamiliar ways. More than anything you want him to touch you again, to bring this dormant need to life.

One of your hands leaves the desk and you almost touch yourself, squirming and writhing with little whimpers before you regain control of yourself. When you look at Sam he's fixed on you like a hawk, eyes narrowing.

"I have to hop off for a few minutes." He says evenly and hangs up the phone without ever looking away. "You're not doing very well."

"I just," you gulp, unsure of what comes next. "I'm sorry."

"Look at how wet you are." He observes casually.

Reaching over he pulls open one of the drawers. Inside there's a folded shirt and two ties. He pulls out one of the ties, rolling it neatly into a ball. He stands up, looming over you, stepping forward between your legs. "Open your mouth."

You obey, dropping your jaw open. He firmly stuffs the tie in your mouth, effectively gagging you. You can't help the desperate moan that gurgles up from your throat.

"Now, stand up and lean over the desk."

You lock eyes for a moment before you comply, standing on shaky legs and bending forward until your belly is pressed against his weekly calendar.

"Arms up here, hands open, palms down."

You stretch your arms up, spreading your fingers over the desk. The skirt is still around your waist, ass on full display.

"Spread your legs wider."

You inch your legs part as far you can. This is a true feeling of utter vulnerability.

"Keep quiet. If you make too much noise someone will hear you."

And with that, his hand comes down on your right butt cheek with a sickening smack that sends your entire body lurching forward. You're grateful for the gag as you let out a muffled cry, summoning every ounce of self-control to stay in place.

There are three more in rapid succession, smack smack smack that sends you careening into a whole new world. It hurts, he's spanking you hard enough his own hand must smart. All you can do is whimper into the gag, dragging your cheek along the hardwood of his desk.

The fifth spank is a quick, nasty slap directly on your bare pussy. It's not a hard as the ones on your backside, but enough to send a spiral of pleasure and pain twisting up your spine as you groan and lift your head.

"You're so wet," his words come out in quick bursts, he's trying to hold himself together. "This desperate little cunt is drooling."

He wipes a wet palm over the stinging skin of your ass and repeats his previous set. Four on your ass and one on your pussy. And then he does it again. And one more time after that.

When it's over you're sweating and crying, tears of frustration, pain and all-consuming arousal. You're right on the edge, you just need him to touch you, all it would take is the brush of his fingers and you'd cum like a freight train.

"Puhhh," you mumble against the gag, fingers clawing the desk.

"You want me to keep going?" He shifts behind you.

"Puhhh," You can't get out anything other than unintelligible sounds.

He spanks your pussy again, only this time it's a lighter touch over your clit. One, two, three little wet whacks that are enough to send you over the edge. You cum, panting with a makeshift gag stuffed in your mouth, bent over his desk, writhing like a bitch in heat.

You're gasping with a cheek pressed into his notepad when you hear the gentle click of a cell phone camera. It's followed by several more accompanied by Sam's satisfied grunt.

"Stand up and turn around." He commands calmly.

Still breathless, you push yourself up with shaking arms, almost losing your balance as you turn to face him. You rest your butt on the edge of the desk and wince. You're not going to be able to sit for a week.

Expressionless, he reaches up, pulling the tie out of your mouth with a yank and throws it back into the open drawer as you close a sore jaw.

He carefully, methodically, reaches forward, the warm tips of his fingers brushing the skin of your breasts as he puts your bra back in place. Long nimble fingers button up your shirt, one by one. Then two big hands, pull your skirt back into place. "Come here."

He places one hand gently on your shoulder, turning you to look into the mirror on the far wall. He's standing behind you, looming like a giant. Your entire face is beet red, cheeks pink and tear-stained, eyes puffy and swollen. The slick between your legs is wet, cold and uncomfortable but a constant reminder of what just occurred.

Your breath finds an even pace while you stare at each other in the mirror.

"If you want this to continue we're going to have to set some ground rules. Is this something you're interested in?" He asks, placing a hand on your shoulder, squeezing as his eyes study the reflection.

"Y-yes." You can barely speak.

"It won't ever be anything more than this, just transactional satisfaction. I'll take what I want when I want it. You understand?"

"Yes." You respond succinctly.

"Good." He gives you one final look and steps away. "Sit down."

He gestures toward the chair across from his desk. You gingerly take a seat, wondering if your ass is going to be black and blue. He scribbles something on a sticky note and hands it to you. It's an address with no context.

"What is this?" You wipe at your cheeks as you clear your throat, finding composure.

"My personal physician. Be there tomorrow at 2:30. I'll have an appointment scheduled for you." He checks his phone, unhappy with whatever he reads and places it screen down on his desk.

"A doctor?"

"I don't leave anything to chance." He rests both forearms on his desk. "I don't fuck with a condom. If you want to take this further, I have certain non-negotiables. I need to know you're on birth control and that you're clean."

You thought you'd reached your capacity for shame but this is a whole new level. You almost choke, clutching both hands together in your lap.

"I-I'm on the pill." It's the only viable thought you can manage.

"That's not good enough for me. You can understand why can't you?" His fingers strum the files on his desk as he awaits your response.

You understand the logic, all you'd have to do is forget to take a pill or skip it on purpose if you wanted to. There's the feminist part of your brain that wants to tell him to get fucked. He can't order you around and assume you're just going to do everything he wants. But there's another part, a stronger part, that actually likes the idea of being controlled. It's not like you can't say no. You could walk out of this building and never look back. He'd let you go.

But offering your submission is your own version of control. You have to comply in order for this to work. It's a two way street and you're the one who gets the final say.

"I understand." You nod, meeting his stare. "I'll be there at 2:30."

"You liked what I just did to you." He cocks his head to the side. "Was it the pain or the humiliation that got you off?"

You gulp, refusing to look away. "Both."

"You are interesting." A smirk crossed his face. "We're going to enjoy each other."

"What else is there? You said you had non-negotiables, was it just the doctor?" You want to know exactly what you're getting yourself into.

"You can't ever tell another living soul about what happens between us." He gets up from his chair and saunters around the desk, sitting on the edge, directly in front of you. "If you want me to stop, you tell me. But once we stop, we won't continue. Ever. You understand?"

"Yes," you nod, watching his fingers curl under the edge of the desk.

"You can't fuck anyone else."

"Alright." You agree. The truth is you'd agree to just about anything to have him touch you again. But there is one term of your own that you need to outline. "What about you? If you expect me to let you…"

"Cum inside you?" His finishes, a hint of amusement in his voice as you blush for the hundredth time.

"Yes." You choke out. "Then I have to be your only partner too."

"Agreed." He shrugs with an easy confirmation. You're not sure its the response you expected but it wasn't tacit acceptance.

"Good." You breathe.

"Good." He mimics, his eyes dropping over your body from head to toe. He leans back and taps the call button on his desk phone. Before you have time to prepare Pepper is bustling into the room.

"Everything alright in here?" She asks coming to stand beside the chair you're sitting in. She gets a look at your face and forces a smile at Sam. You're just thankful she can't see your ass.

"Y/N is going to be working on a special project for me." He disregards her question, getting up to move back behind his desk.

"Special project?" She looks from you to Sam.

"Confidential." Sam looks at you, locking eyes and refusing to look away. There's a now familiar tingle between your legs. "I have an inquiry that I need to keep separate from our other work for proprietary reasons. Y/N has proven her ability to remain discreet. She'll need access to the executive elevator and an all-hours, unrestricted security pass. I'll let you know what else as the situation evolves."

"Of course." Pepper nods. "Anything else?"

"No. You're both free to go." He waves his hands, opening his laptop.

You get up, ready to follow Pepper out of the room but stop for a moment. "Thank you for the opportunity, Mr. Winchester."

His eyes shoot up from the screen, mouth tightening. "I'm sure you'll prove yourself."

With one final look, you walk out of his office. This is surreal, you want to pinch yourself and slap your cheeks just to make sure you're really awake.

"What the fuck was that?" Pepper hisses the minute the door is closed. "You look like a mess. With all the tears I thought he fired you. You're lucky, he hates it when people cry."

"Oh, um," you stumble, looking for a suitable explanation. "He was…rough."

"You have no idea." She rolls her eyes. "What the hell happened at that conference? You said you noted everything and now he's talking about your ability to be discreet and giving you work."

"I can't get into specifics. It's sensitive." One thing is clear, he's never come on to her. She has no idea what's going on behind closed doors, but that doesn't surprise you. Sam has a reputation as a ruthless businessman but you've never heard so much as a peep about anything scandalous. And to be honest he's the last person you would expect it from if it hadn't happened to you.

"Well," Pepper sighs, hands on hips. "I hope you're pleased with yourself. God, you have no idea what you've gotten yourself into. He's a terror to work for, trust me when I tell you that you're not at all capable of meeting his expectations. You won't last a week reporting to him."

"I'm capable of more than you think." You raise your eyebrows, emboldened by this new situation. Sex notwithstanding, reporting directly to Sam gives you a sliver of power, perhaps just enough that she'll ease up.

"Just don't come crying to me when he loses his temper." She laughs dryly. "I'll have your new credentials by the end of the day."

And just like that, your entire life is about to change.


	4. Chapter 4

A week goes by. You do your very best to act like nothing has changed when inside it feels like gravity has reversed. Up is down and right is wrong. Everything is different.

It's just after three on Friday afternoon. Everyone is spread thin and that means he has more on his plate than ever. You've given up on seeing him alone this week, he canceled his monthly employee engagement meeting twice because of the workload, but it's been rescheduled for four o'clock today. Two hours and you'll be out of here for the weekend.

You've moved up the food chain, but only marginally. Afternoon mail delivery is now handled by a mousy college freshman named Bea who's headed in your direction. You're working to finish the current notes when the squeaking wheel on the mail cart stops at your desk.

"Please don't tell me there's more transcription from the Harrison case, I can't handle any more of Joyce's shorthand…"

"I don't have anything interoffice for you - oh wait." Bea crouches down, pulling a padded envelope from the very bottom of the trolley. "This one's for you. I don't know what department it came from."

"Thanks." You take it, turning the feather-light package over in your hands.

There's a small envelope taped to the front that's stamped confidential in bright red block letters. Ensuring no one else is around you open it, removing the single piece of paper from inside.

_Open in private._

That's all it says, but the message is handwritten. This is Sam, it has to be.

Taking the envelope you find an available unisex bathroom and lock yourself inside, checking the door twice. Hands shaking, you tear it open and reach inside only to pull out a pair of red panties. Not exactly a thong, but there's not much to them.

Searching in the envelope you find another note at the bottom.

_Put these on and come to my office._

You haven't worn underwear to work since your last encounter. He'd probably never know but following his rules makes your everyday a little more exciting. You step into your new gift, pulling them into place and throwing away the evidence before making your way to the rear hallway and the executive elevator.

Pepper is sitting at her desk as you approach, glaring at you with confused hostility. "What are doing here?"

"He asked for me." You gesture toward the closed door of Sam's office.

"You're not on his schedule. The hour before the company meeting is always his prep time. No exceptions."

"I don't know what to tell you. He told me to come to his office." You shrug.

"Well, I don't have you on the schedule. Who messaged you? There must have been a mix up-"

"He did." You confirm and she stops what she's doing to stare you.

"Seriously?" Pepper closes her eyes, shaking her head as if it's the most ludicrous

thing she's ever heard. "What the hell does he have you doing for him?"

"I can't talk about it." You maintain composure, despite the excitement growing in your belly. He's right there, on the other side of the wall. You can almost feel him.

"Y/N is here for you." She announces your presence over the intercom. There's an immediate reply.

"Send her in. Hold everything. No interruptions." Sam's voice commands from the small speaker.

Pepper raises her eyebrows, gesturing toward the door.

Sam's standing in the middle of his large office, reading from an iPad. He's rehearsing.

"Hello." The door clicks shut and you stop where you are, standing place.

"Hello." He parrots back, removing his glasses and setting them, along with his tablet, on the coffee table.

He appraises you, looking you over, head to toe as his eyes narrow. "You got a haircut."

"Just a trim." Your fingers twist into the ends of your hair. "Is that a problem?"

"No, but I would prefer if you start wearing it up when you're at work." He studies you thoughtfully. "It can be down, like this, when you're with me."

"Okay," you agree.

"I have one more piece of business we need to get out of the way before we can move forward." He gestures to the paper on the desk. You move to get a better look, only to find it's a contract.

"You want me to sign this?" You look at him, unable to hide your surprise.

"Read it, then sign it." He leans towards you, sliding the paper away from you, almost to the opposite side of the desk.

"Now?"

"Yes." He takes a step closer, his eyes dropping down to your midsection. "Are you wearing what I sent you?"

"Yes."

"Good. Now, why don't you look over the agreement." He turns you around, big hands curling over your hips until you face the desk.

Oh. You get it now.

You have to lean over the desk, your feet nearly leaving the ground, to be able to reach the document. He's quiet behind you as you pull yourself together enough to read the first paragraph. He wasn't kidding, this was a legally binding contract that started with an explanation of how any and all conversations and interactions between the two parties are to be kept confidential.

There are two hands on the outside of your legs, sliding under the hem of your skirt. You suck in a breath, fingers curling against the desk as he begins to lift the material up. "Do you have any questions?"

"I-I um," you skim the rest of the paper. It's basically a gag order, you tell anyone about this little arrangement and Sam can ruin your life. "This is what we talked about before."

"Yes." He purrs, successfully pulling your skirt up over your round little ass. The pads of his fingers trail along the edge of your panties. "Sign it."

You pick up a pen off the desk and scribble your name at the bottom without a second thought.

"You're good at taking orders today." One of his hands grabs the globe of your ass, kneading the flesh. "Stand up and undress, everything except these." He gives you a pat on the ass and you stand up, turning to find him watching you intently.

While he's seen the most intimate parts of your body, he's never seen you naked before. You have to look away from his eyes as you pull your sweater off, then unzip your skirt and step out of it. Willing a steady hand you reach behind your back, unhooking your bra and letting it fall to the ground.

His office is cold and your nipples are rock hard within seconds as you stand there, practically naked, on display. "Would my like me to keep my heels on?"

"What did I say?" His eyes tick up from your breast to give you an annoyed tip of his head.

"Right," you whisper, slipping off your pumps, toes curling into the plush carpet of his office.

"Turn around." He twirls his finger in the air.

Slowly, you rotate in a small circle, letting him have a view of your body from every angle before facing him head-on.

"You have a beautiful body." He comments matter-of-factly.

"Thank you." Your response is barely audible.

Every time you're with him, his very presence elicits anxious arousal that's wholly unique. Despite his demeanor, he makes you feel more wanted than any man you've ever been with.

"Tell me, Y/N. Do you like sucking cock?" A grin tugs at his mouth, one hand shoved in his pocket.

Your entire body goes hot, quaking excitement sparks in your veins. This can go one of two ways, you can melt into a puddle on his expensive carpeting or you can pull yourself together and act as if you've actually seen a penis before.

You find your voice, lifting your chin.

"Yes, I love it." You lock eyes with him.

"We're about to see just how much you love it." His tongue darts out, licking his bottom lip. "Over here, on your knees."

Walking to him you get close enough to smell his aftershave, staring up at him for a second before dutifully dropping down, kneeling at his feet. You reach for his belt, but think better of it. "Should I?"

"Stay just like you are until I tell you to move." He reaches down, trailing his thumb lightly over your cheek before unbuckling his belt, the subtle sounds of leather sliding against metal are all you can hear.

He unzips himself, suit pants dropping to his thighs, revealing plain boxer briefs underneath and the massive bulge of his cock. He palms his erection through his underwear and you watch, spellbound by the sheer size of him.

"Do you want it?" He asks evenly. You wait a moment, before you look upward to find him staring down at you, eyes glazed with lust.

"Yes," your pussy is soaked, aching between your thighs.

"Beg me for it."

You whimper, looking from his face to his hand rubbing his dick.

"Please let me suck your cock." It's forced this first time, you've never actually asked to give a blow job before. But Sam is all about firsts, it's his specialty. The moment the words leave your mouth, there's a throb growing stronger, your empty cunt clenching in anticipation.

"You can do better than that." He shakes his head.

"Please," you sit up a little, looking up at him and giving in to your own need. You do want it and you only have to tell him to get what you want. "Please, I want your cock in my mouth. I wanna choke on you, take you in my throat. Please let me suck your cock."

"That's better." He spits, shoving his boxers out of the way as his dick springs upward, bobbing in front of your face. "Open up."

You don't wait, just wrap your lips around the swollen head of his cock, sucking as if your life depends on it. He grunts and you take it as a sign of approval, sliding your tongue along the underside of his shaft. He's huge, thicker than any man you've encountered before. You'd guessed from his stature that he was well endowed but this is something else altogether.

Cupping his balls in one hand and gripping the base of his length with the other, you begin to bob up and down, taking more and more with each pass. It's not long before he's tapping the back of your throat. Now it's time to show him just how much you really want this.

Taking a breath you prepare yourself for the burn, letting him slide as far down your throat as you can bear. You hold him there, letting the muscles of your throat flutter around his cock before pulling back to take a breath as spit drips down your chin. Two lungfuls of air and you're right back at it, bobbing like before only letting him slide deep with each stroke.

You feel a hand on your hair, twisting his fingers into your locks to get a tight grip. He pulls you back, painfully yanking on your scalp.

"Deep breath." He instructs as you gasp like you're about to dive underwater. He pushes you back onto his cock, shoving his hips forward and lodging himself right back in your throat, holding you there. His free hand reaches down, rubbing over the bulge of his cock in your throat. "Relax. Breathe through your nose and relax."

You manage another two inches, gurgling on his cock, drool running down your chin, eyes watering before he finally releases you.

"I can do better." You sputter, wiping your mouth, looking up at him. "I can take it all."

"Ambitious." He grins, a first genuine expression you've seen so far.

"Please, help me." The words help me trigger something in him, his eyes narrow, mouth tightening.

"You're gonna to stay still while I fuck your mouth, you understand?"

"Yes." You nod, dropping your jaw open and sticking out your tongue. If you didn't feel a whore before there's no escaping it now. It's a feeling that you didn't know you craved, didn't know you needed so badly, until he came along.

He grabs a handful of hair in each hand and forces his cock back into your waiting mouth, punching his hips forward at a comfortable pace. Every third or fourth stroke he pushes deeper and deeper until every thrust is testing your limits. And right when you think you can't take anymore, he pulls you forward, pressing with unrelenting force as you fight the gag and your nose presses into his neatly trimmed pubic hair.

He rewards your efforts by pulling back for a moment before repeating the thrust. Then he does it again and again until your face meets the skin above his cock with every thrust. His soft grunts are closer and closer together. You wonder if he'll cum right down your throat, but just as he's nearing his peak he yanks your head away, leaving you gasping, mouth open and eyes watering.

"Up," he uses his grip on your hair to lift you off the ground, backing you up until he can reach behind your hips to brace his hands on the desk.

He pulls your panties down around your thighs, bending his knees as he jerks himself. The tip of his cock is between your legs, an inch away from your dripping pussy and all you can think about is how badly you wish he'd turn you over and slide inside-

He cums with a muted groan, pressing the head of his dick into the crotch of your panties, shooting pearly ropes of cum until his spunk is thoroughly coating the red lace.

You're panting, chin still wet from sucking his cock as you look down at his seed pooled in your underwear. He leans over, plucking a tissue and wiping the tip of his cock before tucking himself back inside his boxers.

You're frozen as he reaches down and pulls ruined lace back into place, allowing you to feel the obscene wetness of his load pressed against your aching pussy. He pats your cunt twice as if to say job well done before hiking his pants back up.

"Get dressed." He doesn't even look at you, tucking his shirt back in. "If you make it through the meeting without squirming too much, I'll let you cum once it's over."

You can't speak. Sam goes back to reviewing his notes without another word and you wander into the bathroom, taking stock of yourself in the mirror. After several minutes of dabbing at your makeup and smoothing your hair back, you manage to look somewhat presentable but all you can think about is the thick mess between your legs.

When you emerge from the bathroom he's adjusting his glasses in the mirror, glancing up to appraise his handiwork.

"Should I go?" You ask, squeezing your legs together.

"No. You'll stay with me," he instructs as there's a knock on his office door. "Come in."

"It's time. You have to leave now if you want to be on time." Pepper steps inside.

"I'm ready." He confirms, looking to you as he heads out. "Lets go."

"Where do you think you're doing?" Pepper tries to stop you as you follow Sam out the door.

"I need her." He offers with even looking back.

Sam leads the way, walking a breakneck pace as you and Pepper jog behind him.

The auditorium is on the other side of the sprawling campus. This once small law firm has erupted into a multifaceted company specializing in the tech industry, dealing in everything from intellectual property rights to a division known as The Institute that assists in writing policy for political approval.

All of this is Sam's brainchild.

The monthly meeting is less a traditional meeting and more a presentation. A thousand employees pack into the auditorium to listen to Sam talk about the future of the company, where they're headed and how each person is a integral piece of the puzzle. He's an engaging speaker, his success speaks for itself, but seeing him on stage is whole other animal. He's given three TED Talks, each one racking up millions of hits on Youtube.

Other members of the board of directors are often on stage, sitting in chairs, watching and nodding in approval. Pepper is always directly behind him, arms folded into her lap, transfixed or at least faking it.

Someone from IT is hooking a mic pack onto the back of Sam's suit pants as Pepper goes over the last minute changes. It's a few more minutes of prep and then he's ready to address the company. You look around, unsure if you're meant to stay backstage or find a seat in the audience with everyone else, when Sam turns back to you, cocking an eyebrow.

"What are you doing?" He snaps his fingers. "Come on."

"My God." Pepper hisses, grabbing you by the arm and pulling you with her.

By the time you walk out onto the stage there's a smattering of applause rising from the audience. An extra seat is placed next to Pepper's chair and you sit down as Sam begins to speak.

The employees here are engaged. It's a progressive company that offers competitive benefits and obscene salaries for anyone who's willing to work hard and put in the hours. Sam's a son of a bitch and a tough guy to work for, but he puts his money where his mouth his.

There are two spotlights above the stage shining down onto you, hot as the noon time sun. After five minutes you're sweating, and after twenty it takes everything you've got to stay still in your seat. For an hour you do your best to just sit there in front of a thousand people, with Sam's cum wet and warm between your legs.

Just when you think you can't take anymore, there's a round of applause and you realize he's done. You jump up to follow him, happy to be out of the public view. He stops in the wings, turning to Pepper.

"Wait here." He instructs. "Y/N, with me."

There's a small, windowless room to the right of the stage. It's big enough for a table, two chairs and not much else. Sam shuts the door behind you, reaching for a lock but there is none. There are crystal clear voices just outside the room, there's no privacy in here.

"Stand here." He points and you comply, walking toward him, resting your back against the unlocked door. He pulls your skirt up, snaking his hand underneath, wedging between the sticky flesh of your thighs. "Were you paying attention out there?"

His voice is low, just loud enough for you to hear.

"No." You murmur as his fingers slip inside your panties, pressing over the mound of your sex, then lower. "I was so hot I-I couldn't pay attention."

"Is that why?" He smirks, stepping closer. He's sweating, just the same as you, body heat radiating off him. "Next time I expect you to take notes. There'll be a quiz afterward."

"I'll do better." You nod, mouth falling open.

"You have homework this weekend." His eyes are relentless, he's so close you can feel his breath on your cheek. His fingers are playing over your sex, the tips just barely pushing between the lips of your pussy.

"I'm a good student." You mean it honestly and his eyes narrow, looking at your mouth with a carnal hunger that you're getting to know well.

"Every morning, and every night, I want you touch yourself. Make yourself wet but don't cum. No orgasms until the next time I see you. Understood?"

"Understood." You swallow, your pussy throbbing, begging for him to slide inside and offer relief.

"You did well today." He cooes, leaning forward, pressing the weight of his body against you, pinning you to the door. "You're a mess down here. Did this turn you on? Feeling my cum between your legs with everyone watching?"

"Yes." You whimper, legs shivering.

"Do you want me to make you cum now?" His mouth is against your ear, the heat of his body nearly suffocating. He's big and heavy, you couldn't move if you wanted to.

"Yes, please." Panting you try to open your legs further. You want him to shove his fingers inside you, to bend you over and fuck you so hard you won't be able to walk.

"No more talking." He hisses. "Don't make a sound."

His middle finger dips into your cunt, but only enough to wet the tip before finding your clit. He rubs you firm and even, up and down, up and down over your throbbing apex as you struggle to suppress the urge to moan. It doesn't take much, maybe a minute of his finger working diligently until your orgasm builds and explodes. He clamps his free hand over your mouth, the weight of him pushing the breath right of your lungs while you whimper into the palm of his hand, empty cunt clenching again and again.

He removes his finger from your clit, cupping your pussy with his whole hand between your legs, gasping in his hand as he keeps you in place, silent and struggling to stay upright. If he weren't supporting your weight, you'd already be on the floor.

"Say thank you." He whispers, taking his hand away from your mouth, placing it on the wall beside your head. Pulling back he looks at you, that intense gaze that gets you every time. The hand cupping over your sensitive cunt gives a gentle squeeze and you flinch in response.

"T-Thank you." You mutter, throat bobbing, swallowing hard.

"You're welcome." He steps back, relieving you of his hands and body as you nearly wilt to the floor, barely managing to stay upright. He takes a moment, smoothing out his shirt, adjusting his tie before giving you a final look and then he's gone.


	5. Chapter 5

That Friday night, after a quick run and pre-packaged dinner you settle in for a quiet night at home. If you go out, it's always on a Saturday, Fridays are typically reserved for decompression, a little self-care, and Netflix.

It's almost midnight when you finally shut off the TV, but don't move off the couch. Sam's homework has been on your mind since you left, dazed and confused, earlier that afternoon.

It's an interesting prospect, the idea that his control reaches outside of your in-person meetings. He wants to work his way into your everyday routine, little reminders of his ability to get you to follow orders. You don't haveto do anything, he'd probably never know the difference. He's only able to exert as much control as you're willing to give up and you can recognize the power in that.

But there is something appealing about the idea of giving these pieces of yourself to him. There's something about the concept of obeying orders that appeals to a part of your desires that are suddenly alive and vying for control.

Lying back on the couch you snake a hand inside your pajama pants, rubbing your clit, remembering how it felt when he was touching you. It doesn't take long, just a few minutes of letting your mind wander and fingers stoke. It's not long before all too familiar need blossoms between your legs. Dipping a finger into your pussy you're not all surprised at how wet you are. It feels like you've been in a state of arousal since your first encounter, neediness that grows with each passing day.

Using your own slick you go back to touching yourself, bringing your body right to the edge before removing your hand. You give yourself a minute, allowing your body to calm down and then resume the touch, edging yourself again. And then again. You almost cum, it's a close call but right before you're about to tip over that edge you pull your hand away, legs clenched together, teeth sunk into your bottom lip.

That night you lay in bed in frustration, pussy aching with no relief in sight. You don't touch yourself again until the following morning when you complete the task again, edging twice before getting up for the day. By the time the weekend is over you're a desperate mess ready to do just about anything to find relief.

Monday becomes Tuesday and there's still no word from Sam. Attempting to focus on work is a task in and of itself because you're living in constant anticipation of what his next move might be.

"Hey, you." Max is suddenly in your cubicle, sitting on the edge of the desk.

"Hi," you smile, glad for any and all distractions. "Long time, no see."

"I've been working on the Jablonski case. A bunch of us got sent to Orlando for depositions." He shrugs like it's no big deal, but in truth, he loves to peacock. "Trina told me you're working on some hush-hush project with Sam. What the hell does he have you working on?"

He's teasing but he also wants the details. Max is always in everyone's business, it's how he got to where he is. He uses any and all information to his advantage. The last thing you need is him sniffing around.

"I can't talk about it." You mime zipping your lips with your fingers.

"Oh, come on," he places a hand over his heart. "It's me. Give me a hint."

"I can't." You nod succinctly.

"Did you hear he chewed Lacy a new one? I don't know what she did but Pepper said she was hysterical after she left his office. Didn't stop crying for an hour. He's got a real way with people."

"He's got high expectations." You shrug, squeezing your thighs together at thought of your dirty little secret.

"You must have figured out how to work with him. He doesn't tolerate any of us lowly plebs." He grins, leaning closer. "Come on, give me a hint."

"Nope."

"I'll get it outta you." He grins.

Max is all charm. There was a time when you entertained the idea of hooking up with him but those days are long since past. The idea that anyone will ever make you feel as exhilarated as Sam is laughable.

"No, you won't." You tap the desk, spinning the chair back toward the computer. "I really need to finish this."

"What you really need to do is wrap up for the day. Let's go to Lucky's and have a drink, I still owe you one."

Sighing, you look at his lopsided smile. "I don't think that's a good idea."

"Why not? I don't bite, too hard." He's grinning like a wolf.

"Number one," You raise a finger. "I don't date people I work with. Number two, I'm kinda seeing someone."

"Well, as luck would have it, I'm not trying to sleep with you." He makes the sign of a cross over his heart. "And frankly my feelings are hurt that you think I have such salacious motives. I'm nothing if not a gentleman."

"Alright," you roll your eyes. "Enough with the choir boy routine."

"One drink, no ulterior motives. We're friends, that's all." He offers.

The truth is you don't have many friends, certainly no one at work. It would be nice to make an actual connection.

"One drink, nothing else." You warn.

"I swear."

By Thursday you're sure Sam's homework is designed to kill you. You've almost given in half a dozen times, desperate for orgasm but somehow summoning enough resolve to not indulge. But you're not sure how much longer you can keep it up.

Your phone vibrates in your purse and you retrieve it, looking at a text message from an unknown number.

Come to my office. Bring your phone.

You nearly jump out of your seat, phone in hand as you jog to the elevators. Every time you've been with him it's a different experience and today will no doubt be something new.

Pepper's desk is empty and the door to Sam's office is open. You approach, listening to Sam's voice as you pop your head in the door with a gentle knock on the doorframe. Sam's on the phone, but looks up, motioning for you to come inside. Pepper is taking notes, glaring at you from her seat.

"That's fine - I just don't want to get caught up in something we're not prepared for - I understand - That's no problem - I'll see you next week - you too."

He turns to Pepper. "Set up a meeting with him next week. It needs to be in-person, so if he can't come to me I'll need the necessary arrangements to go to California."

"Of course," Pepper nods. "The finance team needs five minutes later this afternoon. Devin wants final approval of several projects before he starts allocating specific budgets."

"Whatever he needs." Sam looks to you, his tongue darting out over his lower lip. "Are you free right now, Y/N?"

"Of course." You offer, afraid to speak to him in front of anyone else. It feels like this secret might tumble out without warning.

"Wonderful." He quips, plucking his suit jacket from the back of the chair. "I'll be back in an hour."

You follow as he walks out of the office, never exactly sure of what he expects. Standing next to him on the elevator you're silent as the door slides closed.

"How are you?" He asks, looking forward.

"Frustrated." You answer honestly.

"Sounds like you completed the tasks I gave you." The comment sounds off-handed as if he's talking about the weather while he adjusts his watch.

"I did." The floors tick by as you descend. "It was…challenging."

"I wouldn't have picked you for my special project if I didn't think you weren't up for a challenge." He turns toward you, looking you over in approval. "Besides, that was just the beginning. We're going to test all kinds of limits."

The elevator dings and you follow him out into the lobby of the main building. People part like the Red Sea, watching him as he strides toward the doors.

"Where are we going?"

"There." He points across the campus to the new construction.

The company is growing at an exponential rate. There's always renovation or new buildings popping up. This building is much smaller than the one you currently work in, it looks to be four or five stories. "Who's going to work here?"

"IT," Sam replies, climbing the stairs as you bound behind him.

There's a construction team breaking for lunch, men sitting on the floor eating sandwiches and McDonald's. The foreman makes his way over to Sam, blueprints in hand.

"Mr. Winchester!" He smiles.

"How's progress?" Sam shakes his hand, looking around the naked room, electric wires hanging from the gutted ceiling.

"Right on schedule." The foreman glances at you before showing Sam the new set of schematics. After several minutes Sam signs off on the upcoming work. "The top floor is finished?"

"Last week. I sent your assistant," he hesitates to look at you. "Your other assistant, the photos. The keycard should work, go check it out."

"I think we will." Sam nods.

–

Sam slides his keycard at the glass doors and they open automatically. There are rows and rows of computers in a bright open space with smaller offices off each side of the room.

"The rest of the building should be ready by the end of the month." He explains, not bothering to turn on the overhead lights. He wanders off toward the back and you follow him into a brightly decorated breakroom. Complete with unused ping pong table and big screen TV. "I thought about moving my office, but I like my current view."

He turns back to look at you, taking a seat on a small couch next to the coffee machine.

"It's nice." It's hard to make small talk, not when all you can think about is whether he'll put his hands on you again. "Why did you bring me here?"

"I wanted to get out of my office." He shrugs, palm ghosting over the crotch of his pants. "Take your clothes off."

_Here we go._

You strip on command, shedding your clothes until you're completely naked, standing in front of him with arms at your sides.

"You wore your hair up." He smiles approvingly.

"Everyday, since you asked me to. Would you like me to take it down?"

He bows his head in confirmation. You pull out the pins holding the bun in place, letting hair fall around your shoulders.

"How many times did you masturbate between the last time you were with me and today?" Sam has a way of asking this kind of filthy question like he wants to know what you're having for lunch.

"Every morning and night, just like you told me to."

"Did you let yourself cum?"

"No."

"What did you think about when you touched yourself?" His head tilts to the side, staring at your tits. You blush, looking at the floor and he corrects you instantly. "Look at me when I'm asking a question."

You snap to attention, a familiar tingle blooming between your legs.

"I thought about the way you touch me, how you talk to me." You have to shift your weight from one foot to the other, feeling vulnerable on multiple levels. "All the things I want you to do to me."

"What kinds of things?" His fingers playing over his belt buckle, eyes never leaving you.

"I want you to touch me, fuck me, cum on me." You force yourself to confess more. "I liked it when you spanked me. I've never experienced pain and sex before. It makes me wonder what else I'd like."

"We're going to find out." His eyes hone in on you, curling a finger for you to come to him. He sits up as you stand in front of him. His hand slides between your legs, slapping your thighs apart. "Wider."

You adjust your stance, as he reaches between your legs, pressing his thumb over your clit. At the pressure your eyes roll back into your head, a whimper escaping.

His thumb continues to rub, while his middle and index finger slide along your slit, pushing in with just the tips. "What do you want most right now?"

"Something inside of me." You whimper, hands clenching at your sides.

"When you were touching yourself, did you fill up your cunt?"

"Yes," You nod. His fingers are stroking lightly over your sex.

"What did you use? Your fingers?" He looks up at you, awaiting a response.

"Yes…and…a vibrator." You manage to choke out.

"From now on, nothing goes in your pussy unless it's my fingers or my cock. Understood?"

"Yes," you nod, teeth sinking into your lower lip.

His hand leaves your body, and you open your eyes, looking down at him. He gets one glance at the desperation on your face and chuckles as he undoes his belt.

"I'm going to let you use my cock." He explains, sliding his slacks down, then his underwear as his thick cock springs upward, curved toward his stomach. "No fucking, just rub your pussy on me until you cum."

You're excited and ashamed but ready to do almost anything to get some relief. "Okay."

He grabs your hips as you straddle his lap. You have to watch to line yourself up, trapping his cock between your crotch and his stomach. You slide your pussy along the underside of his shaft as you roll your hips up and down, coating his length in slick. The feeling of anything other than your own fingers almost does you in with one pass. The swollen crown of his cock catches under the hood of your clit and you let it press back and forth, up and down against the V under the head of his dick before going back to the long strokes, letting the length of him slide between the dripping lips of your cunt.

In no time he's coated in your arousal, allowing you to easily slide over him, your clit throbbing, aching at the constant drag. It takes every ounce of self-restraint not to mount him and sink down on his dick.

"I'm gonna cum." You rasp, bracing as your fingers curl into the thick muscle of his shoulders.

"Go ahead." He grunts, watching intently as you rub yourself up and down his cock.

Pleasure racks every inch of your body with the most intense orgasm you've ever felt in your life. All those early mornings and late nights teasing yourself, culminate in this one burst of pleasure that has you shaking from the force of the release. You can't help the moan that erupts from your throat as you cum so hard you can barely see straight. When it's finally over you slump forward, resting your forehead on his shoulder, pussy twitching and pulsing against his erection.

"Thank you." You whisper and he pats your ass cheek in response.

"You deserve it." He pushes you back, looking you in the eyes. Both his hands cup your jaw, it's a gentle touch that's out of character, but his words make up for it. "Now, get on your knees and suck my cock like a whore."

You blink, empty cunt clenching at the word whore, your body reacting despite the fact that you've just had an earth-shattering orgasm. Slithering off his lap you drop down to your knees between his legs and quickly take him into your mouth.

You can taste yourself as his hand twists into your hair, lifting you up and down on his cock. The first few minutes are just a warm up as you get used to the size of him, taking him further and further into your throat with every pump of your mouth.

When his patience runs thin he takes matters into his own hands, holding your head in place while he fucks up into your mouth for the better part of twenty minutes. When he gets close he holds you down, forcing you to take every inch before finally easing up, letting you suck him at your own pace.

He cums, spurting thick and warm. You swallow immediately, letting him fill your mouth a second time before he's done cumming. Then continue sucking the head of his cock until he grabs your hair and pulls you off his dick.

"Did you swallow it all?" He asks, watching spit drip from your chin.

"Yes." You gasp.

His thumb hooks over your bottom lip, pulling your jaw open. "Let me see."

Opening wide for inspection, you feel his thumb rub over your tongue, sliding into the back of your mouth before releasing you.

"Next time I cum in your mouth I want you to hold it, don't swallow until I tell you." His knuckles slide over your cheek.

"Okay." You whisper. "I will."

"I know." He tucks himself back into his pants. "Tomorrow I want you here by six thirty am. I'll text you instructions in the morning."

It's on the walk back to the main building that you remember his request. "You asked me to bring my phone."

"I did, thank you for reminding me." He holds out his hand for your iPhone. "What's your pin?"

"Um," you hesitate but answer before you think better of it. "Twenty-two, fifty-two, eighteen."

He thumbs in your code and unlocks the screen, opening your text messages.

"Hey!" You protest, reaching toward him. He jerks his hands away, shooting you a look of utter intolerance, raising his eyebrow until you slink back, unhappily crossing your arms. You stand watching as he skims your messages, then opens the thread from the unknown number he texted you from earlier. Opening the contacts he inserts a name before handing it back to you.

"Keith Campbell." You read. "You can't just check my phone, go through my personal things."

"I just did." He looks at you, glancing up to nod at a passing employee. "Don't worry, I have no interest in monitoring your texts. As long as you're sticking our agreement."

"I am." You confirm.

"Then pull yourself together. We're going to have a big day tomorrow."


	6. Chapter 6

You hardly sleep. The anticipation of knowing that you're going to see him early Friday morning is enough to make you vibrate with nervous, jittery energy like a hummingbird in flight. Figuring you might as well use this newfound exhilaration to your advantage, you spend most of the night cleaning your apartment until the bathroom and kitchen are sparkling. It's well past midnight when you finally crawl into bed, lying there, staring at the ceiling and wondering what new experiences tomorrow will bring.

The clock ticks six-thirty but you've already been at your desk for half an hour. With the exception of the security team the place is a ghost town. The ding of your phone echoes in the silence as you nearly jump out of your skin.

_**Keith Campbell: **__Come to my office._

You're up and out of your seat in a heartbeat, hightailing it to the executive elevators. The door to his office is wide open, and you step inside, sunlight pouring in through the floor to ceiling windows. Sam is seated on the sofa in the middle of the room. He looks up, seemingly pleased with your promptness.

"Close the door." He instructs as you turn back. "How are you this morning?"

"I'm," you stop to look at him, hair carefully tucked behind his ears. "A little tired."

"Didn't you sleep well?" He raises an eyebrow in question.

"No, I was…excited for today."

"Let's hope it lives up to expectations. Come, sit there." He points to the armchair across from the couch. You take a seat, crossing both ankles, clasping your hands in your lap. He watches every movement, eyes flitting to each part of your body, taking stock."You will spend the entire day with me. That entails meetings, the business review, all of it. When we're in a room with other people, you'll stand or sit next to me, clear so far?"

"Yes." You nod.

"I'll give you a laptop, you can take notes, something to make yourself look useful. Now, and this is the most important part, you're not to talk to anyone other than me. If someone speaks to you, defer to me. Can you do that?"

"I can." Your mind is already racing with a hundred different uncomfortable scenarios but then there's an undeniable thrill at the idea of complying with this instruction. "I won't speak to anyone but you."

"Excellent. Shall we get started?" His eyes narrow and you know the day will be much more than note taking and structured silence.

"I'm ready."

"Sit back, spread your legs and touch yourself. No orgasm."

Oh, God. You wordlessly pull your skirt up and open your thighs, snaking a hand between them. Sam watches for a moment, emotionless, and then picks up his newspapers and goes back to reading. There's the instant conflicted mix of embarrassment and arousal as you rub your clit while Sam sits across from you, going about his morning as if you're not even in the room.

You've been wet since you woke up, every inch of you alive at the thought of what the day would bring. So it's no surprise that it doesn't take long to get close, cunt clenching as you hold your own pleasure at bay. A moan escapes your lips, small and barely audible but he hones in on it like a hawk.

Glancing up he clears his throat, watching your rub yourself, stopping every third or fourth stroke to keep from cumming.

"I don't like labeling things," He goes back to his paper, as if engaging in casual conversation. "I won't ever tell you that you have rules because all this is your choice. What I do have are expectations. I've already outlined several of them. Can you tell me what they are?"

"Oh god." You groan, slowing your fingers to a glacial pace. "No panties."

"That's one."

"No talking about us."

"I would say that's more of a technicality but I'll give it to you."

Your mind races over your meeting with him yesterday, gasping and dipping your fingers down to wet them with your slick before returning to your clit. "Nothing inside my pussy except your fingers or your cock."

"You were listening." He grins, folding the paper over his lap. "Tell me, is that something you want? To have me inside you?"

"Yes." You stare at him head on, legs beginning to shake.

"We'll see how well you do today." Taking off his glasses he leans forward, getting a better view of your cunt. "Why don't I tell you what I have in mind."

You nod, unable to form words, neck snapping back against the chair.

"Don't stop touching yourself, just slow down and control your body. If you cum without permission, you're not going to like the repercussions."

"I won't." You're determined to show him you can take as much as he can dish out.

"After your first time in my office, when I spanked you, did it hurt afterward?"

"A little," you lock eyes with him. "At first I assumed I'd have bruises but it was just red and that went away pretty fast."

"Did you like the way it felt?"

"I loved it."

"You're going to be doing a lot of sitting today, there are more meetings than usual. So I'm going to spank you so hard you're gonna feel it until Monday. When I'm done spanking you, I'm going to put a plug in your ass. That tight little bottom is going to be sore, and full, until you leave at the end of the day. If you're good and do everything I tell you, I'll let you fuck your pussy with my fingers."

"Thank you, I want that." You reply with a sharp breath and Sam's eyes light up.

You hoped he'd spank you again. It's been on your mind since that first time, but there's always another level with him, that's what really crawls under your skin. You've had anal sex a handful of times, none of it was particularly pleasurable for you, but it's something you'll try if he wants. The truth is you'll do just about anything he asks of you.

"Get up, come over here and lay across my lap." He sets the newspaper on the coffee table as you stand up and walk to him, sticky thighs rubbing together as you move.

Hiking up your skirt you crawl over him, lowering your weight so your belly is over his crotch. He's hard, you can feel that huge cock straining through his suit pants while you wiggle your ass in the air.

"You count." His thumb dips down between your legs, checking to see how wet you are before wiping it on the back of your thigh. He grabs a fist full of your butt cheek with one big, warm hand, giving it a squeeze as his palm comes down on the opposite cheek.

_Crack._

You wince. This first one is harder than anything he did before but the pain instantly blooms into pleasure, skin stinging from his hand.

"One." You count, voice already shaking.

_Crack. Crack._

These two are on the same cheek, two hits in rapid succession in exactly the same spot that makes you see stars, sucking deep breathes.

"Three."

_Crack_.

This is the hardest yet, on your virgin cheek and you squeal, a high pitch yelp that turns into a groan.

"Four." You're sweating, fingers curling into the fabric of the sofa.

"Deep breath," he warns, voice low and even, with his hand rubbing the burning skin. You suck in a breath and then he really gets started.

_Crack. Crack. Crack. Crack. Crack._

They're ungodly hard and incredibly fast, alternating between cheeks until you can feel the tears pool at the corners of your eyes.

"Eight." You whimper.

"Wrong." He corrects you immediately. "That was nine."

_Crack. Crack. Crack. Crack._

Again the spanks come in rapidfire succession, hard enough to draw a bark with each one.

"Th-thirteen." You sputter, tears now falling freely. "It hurts."

"Good." He quips. His hand moves between your legs, searching until he finds your clit, rubbing it with his thumb. After a few well placed strokes, his free hand comes down your ass again.

_Crack._

"Do we need to stop?" His inquiry is accompanied by an increasing pressure over your aching clit.

"No," you nod adamantly. "I can take more. I wanna feel it later."

"You don't disappoint, do you." He smirks.

He alternates between rubbing your clit and spanking your backside until you're squirming on his lap, barely able to lie still. Your butt hurts so bad you feel your heartbeat, the flesh throbbing like a frayed nerve, but he's got you right on the edge. If he'd just rub you a little bit longer you'd cum in an instant.

_Crack._

"Thirty." You cry out, slapping a hand over your own mouth to contain the sob.

Sam places a hand on the back of your thigh, right under your buttocks as his thumbs stills over your clit.

"You should see your ass, you'll be thinking about me all weekend." There's a smirk in his voice, as he leans over, pressing a hand on your lower back to keep you in place. Then the click of a bottle and he's rubbing lotion over your cheeks, big hands massaging the tender flesh. Under any other circumstances, it would feel good, but right now it just stings like a mother fucker. "Are you ready for the next part?"

"Yes." You confirm with the side of your face smashed into the couch cushion.

"Just relax." There's the click of another bottle opening but you don't feel anything until he's pulling your ass cheeks apart. Then the wet, cold press of lubed metal as he presses something against your tight hole. "Don't worry, it's small, just enough to make you feel it….that's it, open up for me…"

It's a firm press, agonizingly slow as the plug stretches you open, wider and wider until the flared end slides inside with a quick burn and then your body is closing around it.

"Oh," you mewl at this new, not unpleasant, sensation.

"You should see yourself." He's got both hands back on your bruised ass, pushing your cheeks together and then pulling them apart. "You're all marked up. And your pussy is so wet you're going to make a mess of this pretty skirt. Better clean you up."

He plucks a Kleenex from the side table and wipes up and down your slit until you're no longer sopping wet.

"Get up." He pats the couch between your legs.

You slide off his lap, settling onto your knees on the couch, sitting back, wincing as your butt meets your heels.

He looks over your face for a moment before reaching up to wipe your tears away with his thumb. "You're beautiful like this. Desperate, frustrated, embarrassed. It's fucking perfect…do you like how this feels? Was it too much?"

"Wasn't too much." You're aching, everything between your legs is begging for release. You have no idea how you're going to make it through the day.

"We're not done yet." He glances at his watch. "But we do need to hurry. Pepper will be here soon. You're going to suck my cock now."

"Okay." You agree eagerly, watching him unbuckle his belt. You're so turned on, the idea of having him in your mouth is almost as appealing as him fucking you.

The moment his cock springs free you curl your fingers around him, leaning down to suck on the swollen crown and stroke him a few times before taking him into your throat. Being hyper-aroused helps, you've little gag reflex at the moment, able to swallow him whole as his hips stutter upward.

His hands curl into your hair, rough grunts coming from above you.

"Good girl, just like that, nice and deep." You suck and bob and stroke him until your jaw feels like it might come unhinged. He's close, you can tell because he's panting and tugging on your hair. "Remember what I said, don't swallow."

"Hmmm." You hum in confirmation, vibrating around his dick and he jerks, cumming hard, pumping hot and thick into your mouth.

You do as your told, keeping your mouth on him until he's done cumming. As soon as he's finished, you pop off his length, wiping your chin with the back of your hand.

"Let me see." Still breathless, he cups your jaw, prying your mouth open with his thumb. You can taste him on your tongue, feeling utterly humiliated as he inspects your mouth full of creamy white.

There's a knock on his office door and you freeze, mouth open and skirt up around your hips. Sam looks you, patting your cheek. "Close your mouth, don't swallow until I tell you. Now pull yourself together and sit up."

You manage to get yourself into a presentable state, sitting next to Sam with your jaw clenched shut as he calls for Pepper.

"Come in."

Your eyes go wide, looking at him in horror and he just grins right back, ticking his jaw as if you're one of the sweetest things he's ever seen.

"Good morning sir, I have your schedule ready and it's a full day! Do you want to-" She stops cold when she sees you.

"Y/N," she snorts. "I didn't realize you were here this morning."

You just shrug, lips glued shut, the taste of Sam filling your mouth.

"Well, doesn't matter I suppose. Would you like me to order you a juice, sir?"

"Yes," Sam nods thoughtfully. "Kale and turmeric, and whatever the spice is that they always add."

"Of course."

"Y/N," Sam turns to you. "Would you like anything?"

You shake your head no.

"I'll go place the order. You have ten minutes before you need to be downstairs." She looks at both of you and walks out of the room.

The second she's no longer in view Sam leans over, close enough for you to feel his breath on your ear.

"Swallow." He instructs. You comply instantly but it's only a second before he's asking for more. "Show me, tongue out."

You turn to him, opening your jaw wide and sticking out your tongue, like a patient proving you took a pill.

"You really are made for this."

The moment you're up and walking your entire lower half is on fire. Your ass is still throbbing and the plug between your cheeks is a small but constant stretch.

The first meeting of the day is short, just a quick review of new building plans and the progress on the construction site where he took you yesterday. You sit next to him, barely able to concentrate on your useless note taking as your butt throbs against the rough fabric of the chair.

Fifteen minutes later you're trotting beside him heading to the next meeting. He stops just outside the conference room. Turning and picking an imaginary piece of lint off your shoulder. "Are you ready?"

"Yes." You nod, clenching your ass, struggling to keep your eyes from fluttering shut. "What is this meeting?"

"The Jablonski case." He explains, heading into the room. You follow him as the chatter of the conference room goes silent.

To your horror you're met with Max, who offers you a sly little smile the moment he sees you. You want to die of embarrassment, sure that he will somehow be able to detect the dirty little game you and Sam are playing.

"Let's get started." Sam takes a seat at the head of the table and you sit next to him, nearly wincing in pain. He really did a number on you, but you can't deny you love this, the feeling of your sore backside and the added bonus of the plug is a constant reminder of Sam and the effect he has on you. You rock to one side, subduing a gasp as you settle back in.

Max is the presenter and you're grateful for the laptop, giving a reason to avoid looking at him for the bulk of the meeting.

Sam doesn't normally spend his time in a case review, it's left to the more seniors members of the legal team, but this is a high profile case. A billionaire client who's been charged with a data protection breach.

You're hyper focused, typing every word Max says. So focused in fact that when Sam leans in to speak, you flinch in surprise. He places the back of his hand over his mouth so that no one can see how close he really is, his lips nearly brushing the shell of your ear.

"How's your ass?" He murmurs, sitting back and looking for your response.

You gulp, looking at the screen and type out: sore.

He nods as if you've just imparted some vital piece of information.

Leaning in one more time, he asks, "are you wet?"

You simply nod in confirmation.

He leaves you alone for the rest of the meeting. Nearly two hours of trying to sit still and play the part of some mysterious assistant. When it finally ends, Sam reviews a few of the details with Harry, a member of the senior legal team.

"Hey," Max slides into the chair beside you.

You smile stiffly.

"I didn't know you were working on this case. You should have told me." He persists, eyes narrowing when you don't respond. "Playing this one close to the vest, huh?" He leans closer, looking at Sam as he whispers. "Think you can get me some time with-"

"She's not working on this case." Sam turns in his chair, looking at Max who sits up straight, eyes widening. "Just a unique project that sometimes requires intense oversight. Tell me Max, how long have you worked for me?"

Sam engages in office small talk with a nervous but excited Max as you sit between them, tight lipped. The lucky thing about being with Sam is that people are much more interested in talking to him, than you. By the time they're done you're squirming in the seat, ass on fire, as Max pats the back of your chair.

"See you later, Y/N." He gives you a little salute and leaves the room. Sam looks from the empty doorway to you, but doesn't say anything.

By the time you are ready to leave the room, you're sure Sam is going to be the death of you. You're flushed with excitement, determined to do as he asked, to remain deserving of the reward. The door to the meeting room shuts behind you, and you hear the click of the lock.

"Hands on the table." He instructs.

You bend over, spreading your palms wide, sliding forward.

"Does it hurt?" He asks, two big hands gently squeezing your cheeks through your skirt.

"Yes," you hiss, turning your head to the side, pressing your cheek against the cool surface of the table. "It's worse than last time."

"Yes, it was." You can almost hear the smile in his voice as he pulls your skirt up over your bum, exposing you to his hands once again. "But you like it?"

"I love it." Your confession is more a yelp as he squeezes both cheeks in tandem sending immediate shocks of pain and pleasure right to your sex.

"How about this?" He carefully pulls your cheeks apart, tapping the head of the butt plug.

"It's different…" You whine as he presses down with his thumb, forcing it just a little deeper. "I can feel it all the time."

"Good." He presses for a few more seconds and then you feel him wrap his finger around it, gently pulling back against your tight ring of muscle. You suck in a breath, wiggling despite giving your best effort to stay still. Then he's pressing inward again, finally tugging harder than before and the plug slips out.

You groan, but remain silent as you hear him digging through his bag and then there's the familiar click of a bottle opening. After a few seconds the re-lubricated tip of the plug is pushed quickly back inside you with a grunt.

"This will get us through to lunch." He pats your ass softly. Just when you think he's done, you feel his hand nudging between your thighs and his thumb is in search of your clit. Spreading your legs further, and inching backward you open up as wide as possible to give him better access as he begins to stroke your bud up and down at a slow, steady pace. "You're always so wet when we're together. Are you always like this?"

"I like the way you make me feel," you manage, mouth gaping open as his thumb continues it's tortuous journey over the most sensitive part of your body.

"The feeling is mutual." He muses, dipping the very tip of his thumb inside your pussy, pressing downward to pull you open for him. It's only a moment before he's back to rubbing with even strokes.

"I'm getting close." You warn him, pleasure coiling in your belly.

"Then we should stop. Don't want to take away from the grand finale." He pulls your skirt down, and turns you around with his hands on your hips, fixated on you with the eyes of a predator. "Open your mouth."

You open up and he slides his thumb between your lips, closing them around his knuckle as you suck your own tart taste off of him. Looking up, you find him watching your mouth, his own lips slightly parted as you swirl your tongue around the pad of his thumb. When he pulls back, he wipes his thumb over your bottom lip, pulling down to see your teeth.

"We really are a good match." He laments, swiping his wet thumb across your cheek bone. "Come on. I'm sure we're already behind schedule and I don't need Pepper pestering me the rest of the day."

You make it to five-thirty. After the mid-afternoon break, where he more or less repeated the same inspection and few minutes of pleasure, you sat through a grueling business review watching the minute ticks by at a glacial pace.

As soon as the meeting is done he's off like a rocket with you scrambling to keep up. You step onto the executive elevator, standing beside him as the doors slide closed. The moment the elevator begins its ascent he reaches over, swiping his key card and punching in a numerical code as the lift comes to an abrupt halt.

Before you have a chance to question what's happening he's pressing you against the wall, pinning you in place with the weight and heat of him.

One of his massive hands cups your breast through the material of your blouse, squeezing and groping with his breath at your temple.

"Oh," you wheeze, a tender wanton whine escaping your lips as he touches you.

His hand leaves your breast just long enough to open your shirt, popping the buttons with such determination you're afraid he might rip them off. That same big, warm hand slides inside your bra, pulling the cup down, then pinching your nipple between his thumb and forefinger.

Your teeth sink into your bottom lip as he presses harder drawing a long low whine out of your throat before taking your whole breast in his hand, massaging firmly. This is the first time he's really touched you. Up until this moment, it's been nothing more than calculated, well-placed touches but now you imagine what it would feel like to have his hands on your body, pulling you to him, exploring your skin. This is fast and urgent in stark contrast to the control you're used to.

His free hand slides between your legs, lifting your skirt as he finds his way between your thighs.

"Are you ready for your reward?" He pulls back to look you. For the first time since this started, he looks as strung out as you do. He's sweating as his tongue darts out to lick his lips.

"Please," you implore, thrashing against the weight of him. You splay your legs wider, the material of your skirt riding up until it slides up your hips of its own volition.

Two thick fingers slide into your cunt, thrusting upward as he fills you for the first time. You've been worked up about this since the night in the hotel room, imagining what it would feel like to have him inside you, stretching you open.

"Fuck," you gasp, banging your head back against the wall of the elevator with a resounding thud.

"Careful," he warns, pulling his fingers almost all the way out of you, leaving just the tips inside. "Fuck yourself until you cum."

You realize what he means. He's not going to do this part for you, instead, you have to bend shaking knees, lowering your desperate pussy onto his fingers. Whimpering, you slide down the wall, his fingers filling you again before mustering the strength to stand back up.

"Come on," he encourages, voice thick with desire. His hand gives your breast a squeeze, fingers curling into flesh "Don't you want it?"

"I want it so bad," you mutter, head rolling to the side.

Pooling every ounce of energy left in your system, you begin to slowly, painstakingly slide up and down, fucking your cunt on his hand like a desperate whore. After the first dozen wobbly attempts your lust begins to take over, giving you a superhuman strength to move faster, until you can hear the wet sound of your pussy taking his fingers.

He rewards your herculean effort by positioning his thumb just right so that with every pass it slides beside your clit, adding to the desperation. You're still trapped between his hot, heavy body and the wall, drenched in sweat as you bounce up and down, up and down.

"Please," rasping, you stop to make sure you don't lose your footing. Both legs are quivering like jello, ready to give out at any moment. "I can't get deep enough like this. Please, fuck me with your fingers."

You're sure he's going to deny you, make you do it yourself. But much to your relief he waits for a beat and then thrusts his fingers so deep in your dripping cunt that he manages to get his knuckles past the lips of your slit. Buried deep inside he brings his thumb to your clit and rubs twice, all while pinching your nipple hard enough to make you cry out.

All it takes is two well place strokes and you cum around his fingers. Everything between your legs begins to throb, cunt tightening around his knuckles, ass clenching around the plug, pulling it deeper inside you. It's intense and brutal, your body violently jerking as the waves of pleasure wash over you from head to toe.

The fingers inside you scissor open, staying wide as he pulls out, drawing every last sensation from your pulsing snatch.

He steps back just enough to let you wilt down the wall until your knees hit the carpet. You're only half aware as he takes his cock out of his pants and shoves it into your mouth. Utterly strung out, you suck out of instinct, looking up to find him staring down, his mouth open in the blatant display of arousal he's allowed himself.

Sam shoves forward a few times, tapping the back of your throat and cums, thick and salty over your tongue, sliding down your throat before you think any better of it. You don't stop, licking the underside of the head, letting the flared crown slip gently between your lips over and over. Eventually, he holds your head in place, letting you suck for another minute before pulling himself free.

Fisting his cock he runs the wet head across your lips, tapping it against your mouth, taking a deep breath and then tucking himself back into his underwear.

You remain on your knees, trying to catch your breath. His hands on your face jolt you back to reality, thumb prying your mouth open.

"You swallowed." He states calmly.

For a moment you don't know what he's talking about and then his list of expectations comes back to you.

"I'm sorry." You murmur, looking up at him. "I don't know if I've ever come that hard before. I couldn't think."

He snorts, chuckling as he reaches down, cupping your elbows to help you stand.

"I'll give you one free pass." He offers calmly, already composed. Your legs nearly give out and he grabs you around the waist, supporting most of your weight. "Are you going to be able to walk?"

"Yes, I just need a minute." You breath, watching him watch you. It's an uncomfortable feeling, having someone scrutinize you this up close and personal. It's a unique brand of intimacy that Sam is well versed in.

When you're able to compose yourself, he carefully goes about his routine of putting back together what he's taken apart. He pulls your skirt down, buttons up your blouse and then carefully wipes at the maraca smudged under your eyes. His thumbs sweep across your cheeks wiping away sweat and tears, then he smoothes your hair back, tucking the few wild strands behind your ears.

"Thank you." You hum lost in the feeling of his hands on your skin.

"You're welcome." He smiles thoughtfully, tilting his head to the side. "You keep the plug in until you get home. It's up to you if you want to use it on your own time."

"Okay." You confirm.

"I'm leaving next Tuesday for San Francisco. You're coming with me." He instructs, stepping away from you, smoothing out his own shirt, then hair.

"I'm looking forward to it." You nod. His tie is askew. Before you stop to think you reach out, adjust the knot until it's back in place. Realizing your actions you wait to see if he'll correct you, but instead, he just watches silently as you slink back beside him.

"Thank you." He remarks touching the tie with two fingers.

"You're welcome."


End file.
